5,6-DIHYDROXYINDOLE CAS#: 3131-52-0; ChemWhat Code: 361747

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name5,6-DIHYDROXYINDOLE
IUPAC Name1H-indole-5,6-diol
Molecular Structure56-DIHYDROXYINDOLE-CAS-3131-52-0
CAS Registry Number 3131-52-0
EINECS Number412-130-9
MDL NumberMFCD00798933
Synonyms1H-indole-5,6-diol, 5,6-dihydroxy-indole, 5,6-dihydroxy indole, 5,6-Dihydroxyindole, 5,6-dihydroxyindol, CAP1194, CP1194
Molecular FormulaC8H7NO2
Molecular Weight149.149
InChIInChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
InChI KeySGNZYJXNUURYCH-UHFFFAOYSA-N
Canonical SMILESC1=CNC2=CC(=C(C=C21)O)O
Patent Information
Patent IDTitlePublication Date
US2008/104774AMMONIA-FREE OXIDATION DYE FOR DYEING KERATIN FIBERS WITH ATMOSPHERIC OSYGEN SERVING AS THE SOLE OXIDIZING AGENT2008
US5275626Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent1994
US5053053Process for dyeing keratinous fibres with a hydroxyindole in combination with a quinone derivative; and novel 1,4-benzoquinones1991
US5205837Product based on inorganic or organic lamellar particles, containing a melanotic pigment, process for preparing it and its use in cosmetics1993

Physical Data

AppearanceWhite crystalline powder
Melting Point, °C Solvent (Melting Point)
137 – 138benzene, petroleum ether
143 – 144benzene, hexane
138 – 139benzene, petroleum ether
140benzene, light petroleum

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1Hdimethylsulfoxide-d6400
Chemical shifts13Cd(4)-methanol100
5,6-DIHYDROXYINDOLE CAS 3131-52-0 HNMR5,6-DIHYDROXYINDOLE CAS 3131-52-0 HNMR
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
BandsKBr3436 – 486 cm**(-1)
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
Spectrummethanol3033340
Absorption maximaethanol222, 276, 2986310, 6310, 5623

Route of Synthesis (ROS)

Route-of-Synthesis-ROS-of-56-DIHYDROXYINDOLE-CAS-3131-52-0
Route of Synthesis(ROS) of 5,6-DIHYDROXYINDOLE CAS#: 3131-52-0
ConditionsYield
With sodium hydroxide; palladium-carbon In water

Experimental Procedure
20 g of 5,6-dihydroxyindoline hydrobromide (86 mmoles) were dissolved in 500 ml of water and 14 g of fumaric acid disodium salt (87 mmoles) and 1.72 g of NaOH (43 mmoles) were successively added to the resulting solution.
After addition of 4 g of 5percent Pd/C, the reaction mixture was refluxed for 1 hour in an inert gas atmosphere.
After filtration, the reaction mixture was continuously extracted for 1 hour with t-butylmethyl ether.
After drying of the organic phase over magnesium sulfate and subsequent filtration, the solvent was removed.
9.8 g (66 mmoles) of 5,6-dihydroxyindole were obtained in the form of a light beige-colored powder, corresponding to a yield of 76.5percent, based on the 5,6-dihydroxyindoline hydrobromide used.
Analysis by HPLC showed that the 5,6-dihydroxyindole thus obtained has a purity of around 98percent.
1 -NMR (250 MHz, DMSO-d6): 6.12 ppm (d, J=3 Hz, 1H); 6.75 ppm (s, 1H); 6.82 ppm (s, 1H); 6.98 ppm (d, J=3 Hz, 1H); Determination of the coupling constants in MeOH-d4.
76.5%

Safety and Hazards

Pictogram(s)corrosionexclamation-markenvironment
SignalDanger
GHS Hazard StatementsH302: Harmful if swallowed [Warning Acute toxicity, oral]
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P391, and P501
(The corresponding statement to each P-code can be found at the?GHS Classification?page.)

Other Data

TransportationClass 9; Packaging Group: III; UN Number: 3077
Under 2- 8°C and away from light
HS Code294200
StorageUnder -15°C and away from light for long term storage
Shelf Life3-6 months(2- 8°C) and 1-2 years( -15°C)
Market PriceUSD 8800/kg
Use Pattern
light-responsive self-tanning composition
self-tanning agent
dye precursor
air-oxidative hair dye

Buy Reagent

No reagent supplier? Send quick inquiry to ChemWhat
Want to be listed here as a reagent supplier? (Paid service) Click here to contact ChemWhat

Approved Manufacturers

Watson Noke Scientific Ltdhttps://www.watsonnoke.com/
Want to be listed as an approved manufacturer (Requires approvement)? Please download and fill out this form and send back to approved-manufacturers@chemwhat.com

Contact Us for Other Help

Contact us for other information or services Click here to contact ChemWhat